Journal
ORGANIC LETTERS
Volume 13, Issue 16, Pages 4426-4429Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201766k
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Funding
- National Natural Science Foundation of China [20972117]
- Program for New Century Excellent Talents in University [NCET-10-0649]
- Ministry of Education [IRT1030]
- 973 Program [2011CB808600]
- SRFDP [20090141110042]
- Fundamental Research Funds for the Central Universities
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The first asymmetric sulfa-Michael addition of thiols to 4,4,4-trifluorocrotonates for the construction of a stereogenic center bearing a unique trifluoromethyl group and a sulfur atom has been achieved in high yields and excellent enantioselectivities with a 1 mol % bifunctional organocatalyst. Subsequent transformation led to the expedient preparation of enantioenriched thiochroman-4-one and the key intermediate of the potent inhibitor of MMP-3, (R)-gamma-trifluoromethyl gamma-sulfone hydroxamate.
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